


Cherry Flavored Lube

by blueprint



Category: Teen Wolf (TV)
Genre: Anal Sex, Attempt at Humor, Awesome Scott, Awkwardness, Casual Sex, Cumplay, Dildos, Enemies to Friends, Face-Fucking, Flavored Lube, M/M, Oral Sex, Sex Toys, experienced stiles, grumpy!Derek, horny!Stiles
Language: English
Status: Completed
Published: 2013-09-11
Updated: 2014-04-11
Packaged: 2017-12-26 07:58:06
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 5,812
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/963497
Author URL: https://archiveofourown.org/users/blueprint/pseuds/blueprint
Summary: <blockquote class="userstuff">
              <p>Stiles discovered Cherry flavored lube in Derek's bathroom. Hilarity ensued(?)</p><p>Actually, no. Stiles didn't find this fucking funny. Not anymore, anyway.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This is definitely not meant to be a love story. Or wasn't meant to be one, anyway. The idea came to me after I wanted to write a different fic altogether then had to go to the drug store and spotted cherry flavored lube. And I giggled, a lot. And then this happened. 
> 
> So not canon it's not even funny. Everyone's alive. 
> 
> Uh, idek. First Teen Wolf fic ever written. I'll just go hide in a corner somewhere.

They had been in the woods, dead of night. They had tracked the rogue Omega to this exact location and Stiles had tagged along, despite Derek's stern warnings not to do so. Whatever, Stiles wasn't gonna let Scott face this batshit insane werewolf with only Derek to his aid. The rest of the pack had wanted to come, but Derek outright refused.

"Stiles, look out!" Derek had shouted.

Stiles looked up and before he could have really grasped what was going on, a jagged object had hit him on the back of the head, causing a sharp pain to course through his skull and for his vision to darken. Suddenly, his muscles weren't functioning properly and the last thing he could somewhat hear were Derek's ferocious growls.

\----

"—ogue's dead, Isaac. We're now waiting for Stiles to wake up now. Yeah. Yeah, love you, too. I'll see you tomorrow."

Stiles blinked back into consciousness and groaned. His head was pounding louder than a set of African drums. He groaned again. _His life_ , seriously.

"Stiles! You're up!" Scott stridently exclaimed. He rushed over to his friend's side, grasping Stiles' hands in his.

It was a little too Grey's Anatomy for Stiles' liking.

"Yeah, dude," he said and yanked his hands away from Scott's, "I'm alive, no need to swoon."

Scott rolled his eyes, "We didn't think you were dead, just worried you'll become a vegetable."

Stiles snorted at that, immediately regretting that action because _ow, head. Hurt._

"Good, idiot's up and talking. Rejoice." Derek said and tossed an ice packet to Scott, who handed it to Stiles. _Oh, sweet relief._

"I'm a valuable member of this pack, Derek—" the werewolf snorted, "- and I don't appreciate being called an idiot."

"Calling it like it is. Are your legs hurting?" Derek pointedly asked.

Both Scott and Stiles looked baffled. "Uh, no? Why?"

"Good. Then you can use them to leave."

Stiles simply glared at him. "Dude, my head is pounding. I am in pain, agony of all shapes and sizes. I'm literally bleeding. Do you really want my dad to see me like this?"

Scott cracked a small smile and turned to Derek, "He has a point."

Derek looked between the two teens. He crossed his arms and huffed. "Go to Scott's then."

Scott shook his head. "You don't get it. Parents, we have them. They ask questions when we bring bleeding teenagers home. Also, does it look like he can get himself together long enough to go anywhere?"

Stiles wanted to nod, but the pain was too great. So he just settled for humming in agreement and raising two thumbs up.

"Fine, but you stay on the couch and you don't go anywhere or use anything without my permission, understood?" Derek said, and pointed an accusatory finger at Stiles.

"Sure, whatever you say," he retorted jadedly. Stiles couldn't bring himself to care about Derek and his macho wolf territory bullshit.

Scott grinned. "I think this is the beginning of a beautiful friendship-"both men groaned in distaste, "-just don't kill each other while I'm away, okay? I'll tell your dad you're staying at my place tonight. My phone's on if you need me."

And then Scott was out the door, thus leaving Stiles and Derek in the most awkward silence ever to awkward.

"So, uh," Stiles began. Perhaps Derek was actually a remarkable conversationalist, one who's wise and thought provoking and will show Stiles the ways of the world with astonishing one liners that will blow his mind for all eternity and the-

 "Tired. Goodnight."

Okay, _no_ then.

Stiles sighed, and tried to will his headache away. Despite having no such luck, he did somehow end up falling asleep on the itchiest couch _ever_.

\---

"Can you, not?" Stiles pleaded. He had been rudely woken up by the sound of an earsplitting juicer. He quickly covered his face with a nearby pillow.

Derek stopped the appliance, "It's good for you."

Stiles wanted to roll his eyes, because, _really?_ But his head was still pounding and any facial expression resulted in a shockwave of pain. He lowered the pillow, "Not right now, it isn't. I feel like my head is being slowly ripped apart."

Derek just shrugged. _Like it was no fucking big deal whatsoever-_

Stiles wanted to scream.

"How are you a morning person? That stumps me." Stiles said, candidly shocked. Derek was an _actual creature of the night._

"I'm not," Derek replied, setting down a glass in front of Stiles. It was something green and ghastly looking. Stiles had to make a face. Derek rolled his eyes. "Just drink it. It might actually make you feel better."

Stiles highly doubted that. But he drank it anyway.

It was gross.

Derek was a stupid head.

"Let me look at your head," Derek ordered, beckoning the younger man to sit upright. Stiles reluctantly sat up, grimacing because he did it too fast. He hissed as Derek's nimble fingers delicately padded the back of his head. "Well, you're not bleeding anymore."

"Good?" What was he supposed to say? His head was still throbbing.

Derek blinked, "Yes, it's good. Can you get up?"

 _Oh, here it goes,_ Stiles thought. He knew Derek would kick him out as soon as he could. "Derek, you can at least let me call Scott to come pick me u—"

"To go shower, idiot. I'm not kicking you out." Derek cut him off, waving his hand dismissively.

"Oh."

At that, Stiles was actually speechless. He didn't really know how to go about this situation.

Derek had always just kind of… hated him being there.

Hated the sight of him.

Hated his face.

His voice. 

His smell.

His clothes.

Everything.

Derek hated Stiles. Derek didn't want Stiles around.

Derek sighed, exasperated, "But if you want to leave so badly, don't let me stop you," he said and then left to his room, slamming the door after him.

 _He's like a fucking teenage girl_ , Stiles thought.

Despite the fact that Stiles should've probably called Scott to come pick him up and be done with it; he, quite foolishly, decided to test out this new development.

And so he actually had gotten up, albeit that took him a solid five minutes because his head turned into a fucking nightclub by then.

_Thump, thump, thump, thump._

He somehow managed to make his way to Derek's bathroom. Which okay, new territory he's never been in, wow. He quickly made a beeline for the medicine cabinet, hoping for something valley-of-the-dolls-esque.

But _no,_ Derek was boring.

Toothpaste, shaving cream, razor-

And whoa, okay. Lube. That was lube. Derek had lube.

And it was _Cherry flavored._

Stiles really couldn't stifle the roaring laugh that came out of his mouth. Headache be dammed.

He stopped himself when he heard an angry knock at the door, "What the hell are you doing in there!"

Stiles yelled back, "Nothing!" before quickly closing the cabinet and making note to tell Scott and Lydia and Allison and Isaac and Erica and really, just, _everyone_.

He then noticed the pack of condoms sitting on top of the sink.

 _XXL_ , because of course that giant ego has got to have a massive cock.

Stiles groaned.

Derek was a dick, with a big dick.

That explained so much.

"Seriously, Stiles, the fuck are you doing in there!" Derek yelled. He sounded livid. Stiles smirked.

And then he decided to fuck around with Derek's head. _Because he wanted to and he could._

His smirk grew wider, "I read somewhere that masturbation can like, cure headaches. Releases endorphins or some shit, so I'm trying that theory right now," Stiles said, and bit down on his lower lip to keep himself from bursting into another round of laughter.

Derek snarled, "No, you're not, Stiles. Otherwise, I would've smelled it."

Stiles almost choked on his spit, "You can smell _that?"_

"May I remind you that I'm a werewolf, with a keen sense of smell? Now shower."

So Stiles did. All the while he mentally slapped himself because he totally forgot about the smell thing and Derek upped him on his own prank.

Derek: 1, Stiles: 0.

\---

Stiles didn't expect to stay at Derek's apartment for so long. At first he just wanted to annoy the shit out of Derek and overstep his welcome. But when 9pm rolled around, he was starting to worry. When Derek decided to go on an all wolfed out run (because, why not, right? Dude is so weird), Stiles finally called Scott.

_"Dude. I've been calling you all day. Where are you?"_

"Sorry man, I shut down my phone. I'm still at Derek's"

_"Why are you still there?"_

"I don't know, Scotty! At first I was just like, testing my luck. But it's like he's not even bothered I'm here."

_"That's weird. Last night he couldn't wait to get you out. Do you want me to come over?"_

"Nah, it's fine. I'll just ask him to drop me off after he comes back from his run. Dude. _Dude._ Guess what I found?" Stiles grinned.

_"A dead body?"_

"No, dumbass. Lube. I fucking found cherry flavored lube in Derek Hale's shower cabinet!"

 _"Holy shit!"_ Scott laughed loudly into the receiver, _"That's amazing, oh my god. What do you think he uses it for?"_

"I—Um. I don't know?" Stiles really didn't want to think what Derek does in his free time with cherry flavored lube, or who with.

_"He must use it on women, though, right? You don't think he's gay or whatever?"_

"I—" This conversation was taking a weird and unexpected turn. "I think so? I mean there's Kate. She's female. But he could, like, be bisexual, I suppose?"

Was he really contemplating the sexual orientation of Derek Hale? Stiles shuddered at the thought.

_"I mean, he could possibly just use it for jerking off. Some guys do that, I don't really get the appeal—"_

"Oh my _god_! Stop! Scott, _stop_ right now! We are not having this conversation. Go back to your strange three-way relationship and don't talk to me ever again."

Scott chuckled. _"Thanks for reminding me, Allison wanted me to come over tonight. I might as well call Isaac too."_

And then the bastard hung up.

Stiles slowly put his phone into his back pocket.

And then it was too quiet, too eerily silent.

And Stiles head was too loud.

Because then it wasn't just your average nightclub. It had turned into a gay nightclub.

 

_Thump, thump, thump, thump._

_\---_


	2. Chapter 2

**Summary for the Chapter:**

> Stiles finds Cherry flavored lube in Derek's bathroom. Hilarity ensued(?)
> 
> Actually, no. Stiles doesn't find this fucking funny. Not anymore, anyway.  
> 

**Notes for the Chapter:**

> So I kind of lied? No /actual/ sex for this part, but this has its porny moments. Also I'm extending this to one more chapter, yay. Thanks for all the feedback and kudos, you guys are awesome. 
> 
> Again, this isn't a love story. It's more of a lust story. They fall deeply, madly, in lust.

Stiles paced back and forth the long corridor. He was trying to will his mind to clear any thoughts of Derek splayed out his bed, hand on his cock, rubbing that cherry lube all ov—

_Stop. Right now._

He was losing his mind and it was all Scott's fault.

Whatever, Derek was straight. Stiles… well, Stiles liked guys, but he didn't like Derek.

He hated him, actually. 

Sure, the guy was good looking.

In a sort of threatening, morose, infuriating kind of way.

Totally not Stiles' type whatsoever.

But.

Damn it, Scott.

Damn that bottle of cherry lube.

And an even bigger damn to that pack of XXL sized condoms.

Stiles tried to sit down on the couch but his leg kept bouncing up, restless. This was not happening. He was not thinking of Derek in… that way. This was too strange, too odd, _too wrong._

_He did have pretty eyes._

"Oh my god!" Stiles yelled out. He was fucked.

_Oh to hell with it._

He stopped resisting his urge to fantasize about the werewolf and just let the floodgate of Derek porn into his sick mind. Thoughts of Derek fisting his cock while fucking himself with a big, black, well lubricated (and cherry flavored) dildo, twisting his wrist just so—

Stiles' cock decided to make itself known.

Agh. His head still throbbed, but he then also had a throbbing erection to deal with.

_What was his life?_

Derek couldn't though.

No.

Derek didn't own a dildo. Definitely not.

Derek was straight. He liked fucking women.

But maybe.

_No._

Stiles quickly shook his head and decided to jerk one out in the shower, and then Derek wouldn't have to get back to the fresh smell of cum in his living room.

On his way to the bathroom he passed by Derek's room. The room's door was _wide open_ , and well, straining hard-on or not--If there was a dildo to be found, he'd find it here.

So Stiles looked through the drawers, the closet, under his bed, and _Jesus, did Derek ever tidy up this place?_ Piles of books were all over the place and— _holy shit, who keeps a big, red dildo in his desk?_

Derek Hale, that's who.

Stiles blinked sporadically. Oh god, Derek liked _dick_. Derek _had_ a dick and Derek _liked_ dick. Stiles groaned.

He took the dildo in his hand and squeezed it; it was firm, yet supple. Stiles gulped; his jeans astringent.

He could—

No—

He couldn't.

Derek would smell it.

That could essentially be a good thing, though. He'd smell Stiles all over his sex toy and think of him when he fucks himself, then he'd wanna fuck Stiles. And all will be well with the world and unicorns existed and pigs could fly and _hell froze over last night._

Still, Stiles wondered if Derek cleans his toy after every use. Because if not, if Stiles could just, lick it, and taste Derek. God, that thought shouldn't be so hot, but it was. He might be able to cum just from that.

In the span of 20 minutes he'd manage to go from completely disliking the guy, to wanting to taste his (surely to be glorious) ass (and dick. Stiles was definitely a dick-taster). Maybe they can have hate-sex? Lots and lots of wonderful hate-sex. Stiles liked that idea. He could get behind that idea. They wouldn't be in it because they liked each other; they would be in it purely for the physical aspect. Stiles had to think how to get Derek on board with that idea. _Now back to his other brilliant idea—_

_Derek's dildo._

_Like a kid in a fucking candy store._

Stiles slowly extended his tongue, eyes focused on the red object in his hands. _Just a little bit closer—_

He then heard glass shatter and a gooey splatter.

_Holy timing batman._

Stiles froze, his tongue had still been extended, but he slowly averted his gaze to look at a reddened Derek. Green glop was splattered on the floor along with fractions of glass, how did he not hear that abysmal juicer?

Derek looked mortified. _Good_ , Stiles thought.

Stiles retracted his tongue back into his mouth, which he snapped shut. Derek had decided that the floor was a  work of art, because he'd found it interesting enough to gawk at _for fucking ever_.

"I-I can explain?" Stiles offered, though he really couldn't. That was the most embarrassed he felt in his entire life.

Derek finally looked up, his jaw was clenched and his brow furrowed. He was clearly changing his tactics. "The fuck. Are you doing?" He growled.

"I-I'm 16?" the teen said. Because it was true. He was 16, and horny. He then promptly dropped the dildo to the floor. It bounced a little and made Derek flinch. Stiles rubbed the back of his neck and decided not to look anywhere near Derek's eyes. He finally took a deep breath and decided to tell the truth. All of it. Sans hard-on and hate-sex.

"I'm sorry, okay? But like, I found your cherry flavored lube, man. In the shower cabinet. And I had to tell Scott, because he's my best friend, okay? And we laughed, at first. But then he was like 'do you think he likes dudes?' and I was like 'noooo' but then I couldn't really stop thinking about it? And Scott's a bastard, I swear. And I just kept thinking about what you do with that bottle of lube and other. Things. And I just wanted to forget about it, y'know? Because it's weird. You're weird. But then I walked pass your bedroom and like, I don't know, man. I just wanted to see if like, you had, some sort of sex toy you use the lube on because by then my mind was on overdrive so I kind of, uh, decided to look for it? Which I know is so, so wrong, and I'm so fucking sorry, you don't even know, but then like. I found it. And uh, I kind of wanted to, uh. Like." Stiles finally stopped and had to swallow. This wasn't going well.

Derek stared at him, yet again, mortified. "You wanted. To taste my," he gulped, then quietly said "dildo?"

Stiles decided to play it cool. He shrugged. "Yeah, whatever. It's no big deal." His voice cracked mid-sentence.

He was not playing it cool.

Derek looked thoughtful for a second, before looking Stiles straight in the eye, "Right. No big deal."

Stiles gaped at him.

Was Stiles really getting off the hook? Were pigs flaying? Was hell freezing? Were there unicorns waiting for him?

No, of course not, because he's _Stiles_ and this is his fucked up life.

Derek continued, "It's no big deal, Stiles, _to me_ —" Stiles cringed at how much Derek emphasized the last part of the sentence. Low blow. "—but it's clearly a big deal to you."

And wow, he'd been right. Derek was a huge dick.

Stiles huffed, "You ain't all that, sugarplums."

And then Derek was _smirking_. What the hell. He'd gone from embarrassed, to mortified, to threatening, back to mortified then to fucking predatory in less than 5 minutes. Derek was literally a rollercoaster of emotion.

"Only, I think I am. _For you_ ," Derek said, and walked closer to where Stiles stood. For a second, Stiles thought he was gonna hit him –kiss him maybe?—but he just bent over (really slowly and fuck, his ass looked _amazing_ in those jeans) and picked up the red dildo. He then handed it over to Stiles, who just blinked, because what the fuck? "Go on, you want to taste it—then do it. I hadn't washed it since the last time I used it."

Derek was totally pulling his chain.

Derek: 2, Stiles: 0.

"Ha, ha, ha. You got me, Derek. This is payback for this morning, right? You got me."

Derek just looked somber. "I'm not kidding, Stiles. You want to taste it, then do it. I'm not going to stop you."

Stiles' world was making less sense by the minute.

He swallowed and took the _thing_ from Derek's grasp, who was watching him, intently.

_Alright, two can play this game._

So Stiles, not leaving Derek's gaze, ran his tongue from the base all the way to tip, making sure to swirl his tongue around it. _Shit._ It tasted bitter and salty.

Derek's expression was stoic, not giving anything away. Stiles had been doing his best tricks- licking, nipping, coating this thing in his saliva-

His eyes _smoldered_ for fuck's sake.

Stiles let out a guttural moan, his mouth stretched wide over the red tip. He wasn't above making obscene noises.

_That'll get the werewolf going._

"You done?" Derek said after a brief minute, looking absolutely bored.

Stiles let the dildo out with a 'pop', a trail of spit hanging from his mouth. "Really? That didn't do anything to you?"

Derek snorted. "You sure think highly of yourself if you think that's enough to get me hard."

Derek was clearly challenging him. Stiles may not be a GQ model but he knew he was attractive, goddamn it. And _hate -ex_. This could lead into fantastic hate-sex, why couldn't Derek see that?

Maybe Derek wasn't one for the visual (or audio. Which was absurd because  _werewolf_ ), maybe he needed a more forthright approach.

Stiles discarded the dildo behind him, cringing when he heard it knock over a pile of books on the desk. He then sunk down to his knees. Derek in turn glared at him. "The hell are you doing now?"

The teen gazed up under his lashes to look at him, biting his lower lip in the process. "Fuck my mouth."

Derek kept himself stoic. "I'd rather fuck a tree."

"Why are you denying this, Derek? We clearly have this feral, crazy, sexual-"

"-If you say tension, I will kick you in the goddamn balls. I'm not denying anything. I don't think of you that way. So you found out I'm also attracted to guys, so freaking what? Doesn't mean I'd fuck anything that moves and has a cock."

Stiles lowered his gaze, his ego well beyond busted. He'd been rejected before, but this fucking _stung_. He quickly got up and brushed off invisible dirt, "You're right. Sorry." He solemnly said.

Derek sighed, his expression softened, "Look, I probably do care about you, a little. Very little, in fact. But me slamming you against walls isn't because I want to fuck you, Stiles. It's because you seriously annoy me."

Stiles whined, "That's the point, though! We're supposed to have mad, wild hate-sex." He finally let slipped.

Derek looked taken aback, "What? You don't like me?"

Stiles huffed. "Have you _met_ you? You're kind of insufferable. And weird. _So fucking weird_."

"So what was all of this? The 'fuck my mouth' thing? You going to town on my," Derek lowered his gaze and quietly whispered. "Dildo?"

Stiles nearly cooed. Big bad wolfy was almost adorable.

"That was me trying to seduce you, jeez. Not everything has to do with _feelings_ and _emotions_ and whatnot. You're hot, I'm somewhat attractive. Let's fuck."

Derek blinked. "I-okay."

Stiles blinked back. "Wait, really?"

"Just sex?" Derek clarified.

"Just sex." Stiles confirmed.

_Just exceptionally hot hate-sex._


	3. Chapter 3

**Notes for the Chapter:**

> Got blocked on this story, but for some reason got inspired to finish it today. So uh, sorry it took so long! I suggest re-reading the first two chapters if you've read it already. 
> 
> This turned out kind of fluffy. Eh.

"No one can know about this," Derek said as he pulled his shirt over his head, tossing it aside. 

Stiles blinked at him "Dude, why would I tell this to anyone?" he said and stepped out of his jeans, kicking them and then swiftly unzipping and shedding his hoodie.

Derek glowered. "Your mouth is known to say inappropriate things in the past."

The teen shrugged. "Nah, this will be our dirty little secret. Trust me, I don't want anyone knowing this as much as you do."

Derek finally shimmied out of his sweats, leaving him in a pair of boxer briefs. 

Eh, he didn't seem the type. 

But then he took them off, too, and hello. Derek's dick definitely warranted a pack of XXL condoms. Stiles mimicked his actions and then they were both naked. 

Finally. 

"I mean it, Stiles. Don't tell anyone. Not Scott-"

"-Wouldn't dare."

" Or your dad-"

"-Please, what do you take me for?"

"-Not anyone." Derek was wide eyed and pursed lipped. He pointed decisively at Stiles, "Got it?

Stiles snorted, "Yeah, yeah, I got it." He said and climbed onto the bed, reclining on both his hands as he spread his leg, unashamed. "Now come mount me, sourwolf."

Derek rolled his eyes, "You're not so good at dirty talk, you know that?" he said, amused. "I'll be right back."

Stiles assumed he was going to retrieve the condoms and cherry flavored lube from the bathroom so he didn't question him further. He slowly began caressing his skin, bringing a finger down to tease at his dry entrance. Eyes closed, he let the ambiance envelope him, his body becoming increasingly hotter. He was so turned on by his hands, and just, the entire situation. As surreal as it seemed a mere 24 hours ago, he was just over the moon it was actually happening. Fucking Derek Hale, whowouldathunkit?

The deep growl he heard made him smirk, humming his approval.

"Bet I'm making you hard now." He made reference to what the werewolf said earlier. When he didn't immediately get a response, his eyes opened to a sight he vowed to forever keep in store his spank bank. Derek Hale, eyes locked on him while fisting his cock. Heated skin and eyes, a predator at least. And fuck yes, he was hard. And still so very huge. Stiles didn't even know if the tip could breach him, let alone that entire length.

"I'm probably going to regret this," Derek said, sauntering over to where Stiles was sprawled on his bed. He should have probably taken some offense in that statement, but the feeling was mutual.

"Ditto," he simply replied. But there was no going back now. That dick, slathered in that lube, covered by that condom – was going in him like, two minutes ago. Derek tossed him the bottle, it bounced a little by his head. Stiles stared at it. Uh.

"Prep yourself."

"Holy hell, could you be any lazier?" he asked, dumbfounded. 

The older man sat down next to him, loosely stroking his cock and eyes seared into Stiles' own. "I wanna watch."

And oh. 

_Oh._

Kinky motherfucker. 

Stiles grinned, "And you tried to deny our feral, crazy, sexy-"

"Goddamn balls, Stiles. Goddamn balls."

The teen snickered but proceeded to grab the bottle and pop the cap, pouring the lube onto his fingers. He made sure the lube was warm enough before guiding his fingers down his happy trail, over his hard cock. He teased a bit at his taint, letting out a shuddery moan before finally reaching his tight ring of muscle. He kept one finger circling his hole, his breathing becoming shallower. 

When he looked over, Derek looked absolutely _wrecked._

The man before him looked so hot, so open. It was such a contrast to the closed off Derek, he had a hard time perceiving it as reality. And maybe it wasn't, maybe it was a dream. Maybe he'd died from that head wound and this was the afterlife.

Both those theories sounded more legit than the reality happening before his eyes.

"Still want me to fuck your mouth?" Derek asked on a breath and holy fuck.

Did he-

What-

Stiles had to grip himself so he wouldn't come. Derek clearly noticed and chuckled. "I take that as a yes, then."

Stiles swallowed. He had one finger inside himself, avoiding his prostate on purpose. Did he want Derek to fuck his mouth? He-

He kind of did. 

He'd never done it before though, so.

Uh. 

"I do. But. I never had anyone do that to me before, so you'll have to go slow."

Derek moaned loudly at that. Macho werewolf territory bullshit.

"So uh, how do you want do this?" 

"Just, lay down."

Stiles scooted down, his head now in the middle of the bed. He'd gotten two fingers in his ass, though he ceased movement. In a flash, Derek was on him. Stiles let a very manly squeak.

Very manly. 

The manliest.

Derek grinned down on him wolfishly. And wasn't that fucking dandy? Stiles stared at him, wide-eyed and beyond turned on. He teased his entrance with another finger, getting just the tip in. 

Stiles closed his eyes, willing himself not to come and stay focused enough to make this last. When he opened his eyes, he had a monster cock in his face. Fucking-

Derek thrust his hips forward lightly, the tip of his dick nudging at his closed mouth. 

Stiles was no longer as impressed. He glared upwards, "Really?"

Derek smirked down, "Thought you might want a taste."

"Don't flirt, honey. I'm a sure thing," he deadpanned. 

"I'm still a gentleman."

Stiles snorted. This flirting-

Oh god, they were flirting. They weren't supposed to flirt. They were supposed to grunt at each other and yell and call each other "Bitch!" and "Jerk!" and what have you. 

Stiles looked behind Derek's shoulder. Maybe this was a mistake?

Derek growled, "You're overthinking this."

Stiles refocused his attention. How did this even happen? Was he that controlled by his dick? "You're not thinking enough."

Derek looked agitated. "This was your idea, Stiles."

"You're the adult here, Derek. I'm the kid; I shouldn't be the one calling the shots."

Despite Stiles' change of heart, Derek made no beeline to move. Instead his gaze on him softened. "You're right. But I believe you're far more mature than you allow yourself to think, this could honestly just be for fun. Something I think we both need."

Derek was-

Derek was making sense.

Stiles breathed in deep, and nodded, "Yeah, yeah, you're right."

Derek smiled. For the first time it wasn't predatory, or smug – it was genuine. 

(When Stiles will reflect back on this moment, he'll conclude this was the moment they became actual friends. Crazy as it sounds, just friends.)

He smiled back at him. "So are you gonna fuck my mouth?" 

The older chuckled and gripped himself, "Gladly."

Stiles was three fingers in, and despite how his body tensed up during his moment of hesitation, he was feeling pretty open. His dick wasn't as hard as it was when they first started, but it hasn't gone down completely.

Stiles opened his mouth and Derek guided himself inside, sighing as the tip brushed over Stiles' tongue. The taste of precum made his taste buds tingle, the feeling of something that hot and heavy in his mouth shoot straight to his cock and the little guy stood at attention. Proud papa.

Derek eased in a bit more, though they both knew there was no way his cock could go all the way down Stiles' throat. He started movement, going slowly and giving Stiles some leeway in between thrusts.

He could see Derek was struggling to maintain composure, the dude probably wanted to fuck his face raw, but knew Stiles wasn't ready for that.

As Derek's breathing became more ragged, and as Stiles fingers dug deeper – Stiles had a moment of revelation. This, whatever this was, it was about trust.

They had grown to trust each other. Wholeheartedly. 

Stiles hadn't experienced this level of trust with anyone who wasn't his Dad or Scott. 

Huh. Well, wasn't that a turn of fucking events?

"I-shit. I gotta fuck you, Stiles-" he stopped to swallow and extract himself, "Please tell me you're ready."

That desperation in Derek's voice officially made his dick rock hard. And his grin completely smug, "Like I said, mount me, sourwolf."

Derek rolled his eyes but the fondness was there. There was no going back, they were friends. Best friends, even. "As you wish."

"No Princess Bride quoting, bro. I might actually think you're awesome or whatever."

The werewolf actually laughed at that and scooted down to position himself between the v of Stiles' legs. Guess they're doing this missionary. Stiles retreated his fingers; they've been in his ass long enough. After wiping his hand on the sheets (to which Derek made a disgusted face. Which, really? Guy digested disgusting green goo every day, this made him grossed out?), Derek grabbed a condom and rolled it down, giving himself a few strokes before lining himself up to Stiles' entrance before meeting his eyes. "I'm going to be inside you now. And this won't be your idea of hate-sex, I'm going to make this good for both of us, and after, this won't be weird or awkward. It'll just be what it is."

Stiles let out a breath and blinked. "Why aren't you this sensible all the time?"

Derek tilted his head sideways, mouth quirking up, "I honestly don't know."

They both cracked up, and Stiles decided he liked this. This vulnerability they were sharing with each other felt new and different but also right. Like they were always meant to be this close and open.

"Okay?"

"Okay."

Derek bracketed Stiles' head with his hands, the other's legs wrapping around his waist as he pushed inside, Stiles' hole giving in a little too easily. But he honestly never felt this relaxed in his life. It burned, yes. Derek was still abnormally huge and he didn't fully bottom out before moving his hips, pulling out and slowly thrusting back inside. Stiles let out a gasp as he felt himself opening up and letting Derek go in deeper. 

Derek let his forehead slump down on Stiles' shoulder, moans spilling on Stiles' skin. The teen wasn't as discrete though, as he groaned and moaned his approval. 

Then Derek hit his prostate dead on and holy-

"Shit! Holy shit, Derek."

Stiles felt rather than heard Derek's laughter.

Stiles whined, in a very manly way.

Very manly. 

The manliest.

"You dirtbag, don't laugh at me."

Derek looked up, face red and split on a grin, "I'm not."

Stiles attempted to glare. As best as he could with a massive dick up his ass.

Derek then proceeded to apologize.

With his dick. 

"Fuck you," Stiles said with no heat. 

Derek stopped his movement, "Next time."

Fucking-

What.

"Dude. Don't say stuff like that if you don't mean it."

Derek just smirked as he kept thrusting. Bastard. His pace wasn't as rapid as Stiles had predicted it to be, but he was thankful for it. His asshole probably wasn't up to getting ripped open, but this was good. It was slow and caring even. And his prostate got her fill (it was a she, he called it Selena. Don't ask), and it appeared that Derek got his, too. If his moans and grunts were any indication.

"Stiles, I'm-I'm close."

"Yeah, yeah, okay."

Stiles grabbed his dick and started stroking feverishly, feeling himself getting closer to the edge. Derek pulled out, causing Stiles to whine (again, very manly), because why? Stiles began to feel himself getting close, too. Did Derek really have to return to his douchebag mode in that exact moment? 

"Can I come on you?"

And-

What.

Macho werewolf territory bullshit. 

Hot. That was hot. Why was that hot?

"Yeah. Fuck. Yes," he said, his hand now flying over his dick. Derek removed the condom and also began his own frantic strokes. God, how was this real life. Derek gasped as white ropes flew from his cock and landed on Stiles' abdomen, some landing on his collarbone. He felt the tightness of his balls before he found his own release, his cum mixing in with Derek's on himself. 

Derek collapsed on top of him and Stiles had two thoughts going in his head.

1.Best. Orgasm. Ever.

2\. Can't breathe.

"Heavy, dude. You're too heavy," He choked out, feeling the weight of the other man on his windpipe. 

Derek chuckled and rolled over, they both had cum on this chests and stomachs and even though that was so majorly gross on so many levels, Stiles still thought it was majorly hot.

Uh, cumplay. That was apparently a _thing_.

"So, we just had sex," Stiles said after a minute, feeling the afterglow wearing off.

"And it felt so good?"

Stiles' head swiveled sideways. Did he just-

_No._

Not possible.

"Did you just-"

Derek just wiggled his eyebrows and smirked. Stiles had to laugh.

"You're awesome, bro."

"Ditto."

Scott was right, this was the beginning of a beautiful friendship.

**Notes for the Chapter:**

> I wanna try taking prompts on tumblr, so hit me up with one on http://heysugarbaby.tumblr.com/

**Author's Note:**

> Yay? Nay? Oi vay.


End file.
